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Going, Going...

The greatest baseball player in the world is about to lead the game’s most storied franchise to its thirteenth consecutive October in the playoffs. And then he might leave town. Inside A-Rod’s Endgame.

The last time the New York Yankees didn’t make the postseason, there was no postseason. It was 1994, the year a strike canceled the World Series. The Yankees’ closer was Steve Howe, who is now dead, and their two hottest minor-league prospects were Derek Jeter and Mariano Rivera. The team has spent the last twelve Octobers freezing deep into the night in front of a tense, Rudy Giuliani–led crowd. But this year looked to be different, even in the context of other recent early-season scares. They fell 14.5 games behind the Red Sox in May. Stars like Mike Mussina, Jason Giambi, and Johnny Damon have suffered some of the worst years of their careers. The pitching staff has included gentlemen named Matt DeSalvo, Jeff Karstens, and Chase Wright. The signing of Roger Clemens was announced with immense fanfare, but the Yankees will end up having paid about $18 million for less than twenty starts of average pitching from a 45-year-old man.

Given all that, at press time, the statistical analysts at the Website Baseball Prospectus list the Yankees as having a 99 percent chance of making the playoffs. And though the Yankees have drawn some life from portly Nebraskan relief wunderkind Joba Chamberlain and resurgent veterans Andy Pettitte and Jorge Posada, the real reason they’re headed to the postseason again is third-baseman Alex Rodriguez—baseball’s best player, a lock for the American League MVP award, a superstar having the best season of a career that would already put him in the Hall of Fame even though he has years left in his prime. Without Rodriguez, the Yankees would be lost; with him, they could win it all.

Yet in less than a month and a half, there’s a chance he could opt out of his contract—the biggest in sports history—and voluntarily leave baseball’s wealthiest and most successful team. It depends on how Rodriguez plays in the postseason; it depends on how a cadre of Yankees insiders in the dawn of the post-Steinbrenner era can work with A-Rod’s agent, Scott Boras. If Rodriguez leaves, the repercussions for the future of the Yankees organization could be enormous. And in the end, what happens might depend less on the actions of any one person than it will on the mood at Yankee Stadium the moment the team finishes its last inning of the year.

For the particular timing of this dramatic situation, we can thank Scott Boras. The Über-agent is Rodriguez’s longest-standing comrade in baseball—A-Rod has been represented by Boras since he was drafted at age 17. Boras is arguably the sport’s dominant economic force. His agency, the intimidatingly named Boras Corporation, has been called the “31st franchise”; if its top clients were on a team together, they’d earn $253 million a year total ($55 million more than the Yankees) and easily be the best squad in the game. He’s single-handedly revolutionized the amateur draft with a simple strategy—if his clients’ salary requirements aren’t met, they sit out and reenter the draft the next year. He’s negotiated the largest contract in history for a player entering the league from Japan (the Red Sox’s Daisuke Matsuzaka). And, of course, he’s negotiated the biggest contract in sports history—the $252 million, ten-year deal that Rodriguez received from Texas Rangers owner Tom Hicks in 2000.

In that transaction, A-Rod got everything he could have possibly wanted, but when the Rangers failed to finish above. 500 in three years with him on the team, he also got a reputation as a mercenary whose salary had crippled his team’s ability to pay the other players needed to win games. It’s arguable: Maybe the Rangers could’ve found better teammates for the same price, and maybe they could’ve spent more thanks to the revenue A-Rod brought in. Regardless, the boos started to rain down in Texas, and Boras looked for a way out. The Red Sox were very close to finishing a trade, and Rodriguez had even agreed to lower the overall value of his contract in order to make things work, but the Players Association objected and the deal fell through in December 2003.

The Yankees stepped in two months later, of course, and nabbed him. Hicks agreed to pay close to $10 million per year of A-Rod’s contract. That made Rodriguez relatively cheap for the Yankees. But back in 2000, Boras had thought to include a clause allowing A-Rod, after seven years, to opt out of the contract and become a free agent.

Given Boras’s style—which has been called “ruthless,” but in the incompetence-plagued world of pro-baseball management might be better described as “not boneheaded”—and simple common sense, the possibility seems small that Rodriguez, after the best year of his career, won’t sell high. And there are plenty of teams out there ready to bid for his services. The leading competitors are the Red Sox and the Chicago Cubs. Other, less likely possibilities include both Los Angeles franchises, the Detroit Tigers, and, if they can figure out a place to play him, the Mets.